2002 Fiscal Year Final Research Report Summary
Synthetic Chemistry and Materials Chemistry of Functionalized Fullerenes
| Project/Area Number |
13440187
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Hokkaido University |
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Principal Investigator |
MASAYA Sawamura Hokkaido University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (40202105)
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| Project Period (FY) |
2001 – 2002
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| Keywords | Fullerene / Ferrocene / Vesicle / Liquid Crystal / Organocopper / Cbo / C70 / Functional Materials |
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| Research Abstract |
During our studies on fullerene functionalization, we have found a one-step five-fold addition of a phenylcopper(I) reagent to [60]fullerene. This reaction produces a.cyclopenadiene embedded in a spherical surface of [60]fullerene. The cyclopentadiene in the new molecule consists of one of the twelve pentagon of [60]fullerene, and is surrounded by the five sp3 carbon atoms bearing a phenyl substituent derived from the organocopper reagent. The cyclopentadiene structure can be converted into 6-π electron cyclopentadienyl anion through deprotonation by a base. Metal complexes containing a five-carbon ligand cyclopentadienyl (Cp) play very important roles in organometallic chemistry. This study aimed at synthesis of functional molecules useful for applications as catalysts and materials by means of such functionalized fullerenes.
As results of this study, the multiple addition of organocopper reagents to fullerenes have been significantly improved so that various fullerene derivatives with different organic substituents can be synthesized in quantitative yields in large scales. Hybrids of fullerenes (C60 and C70) and ferrocene were synthesized. It was found that alkali metal salts of the cyclopentadienyl type-fullerenes are soluble in water and that they forms spherical bilayer vesicles. Derivatives with liquid crystalline properties and double decker Cp-type compounds were also synthesized.
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